N-aroyloxynaphthalimides as novel highly efficient DNA photocleavers:: substituent effects

被引：14

作者：

Qian, XH ^{[1
]}

Yao, W

Chen, G

Huang, XY

Mao, P

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China

[2] E China Univ Sci & Technol, Inst Pesticides & Pharmaceut, Shanghai 200237, Peoples R China

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 35期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/S0040-4039(01)01214-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel DNA photocleaver family of N-benzovloxythioxonaphthalimides. which show improved DNA intercalation and photocleaving activity compared with their oxo- counterparts, were synthesized and evaluated. The substituents on the benzene ring of the benzoyloxy moiety have an important and unusual influence on the DNA photocleaving activity. N-(p-Methoxylbenzovloxy)thioxonaphthalimide is able to photocleave DNA at low concentration (5 muM) with 'time-resolved' and pH independent properties. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6175 / 6178

页数：4

共 18 条

[11] PHOTOINDUCED DNA CLEAVAGE VIA ELECTRON-TRANSFER - DEMONSTRATION THAT GUANINE RESIDUES LOCATED 5' TO GUANINE ARE THE MOST ELECTRON-DONATING SITES [J].

SAITO, I ;

TAKAYAMA, M ;

SUGIYAMA, H ;

NAKATANI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (23) :6406-6407

[12]

SIGMAN DS, 1993, NATURE, V364, P474

[13]

SINGER P, 1987, J BIOL CHEM, V262, P14478

[14] 1,8-naphthalimide hydroperoxides as novel intercalating DNA cleavers [J].

Tao, ZF ;

Qian, XH ;

Wei, DZ .

DYES AND PIGMENTS, 1996, 31 (03) :245-251

[15] On the mechanism of photo-induced nucleic acid cleavage using N-aroyloxy-2-thiopyridones [J].

Theodorakis, EA ;

Xin, XA ;

Lee, MD ;

Gibson, T .

TETRAHEDRON LETTERS, 1998, 39 (21) :3383-3386

[16]

THEODORAKIS EA, 1997, J CHEM SOC CHEM COMM, P1463

[17] Synthesis of fluorine-containing oxazolonaphthalimide hydroperoxides as DNA photocleavers [J].

Yao, W ;

Qian, XH .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 106 (01) :69-72

[18] Novel and highly efficient DNA photocleavers: hydroperoxides of heterocyclic-fused naphthalimides [J].

Yao, W ;

Qian, XH ;

Hu, QY .

TETRAHEDRON LETTERS, 2000, 41 (40) :7711-7715

← 1 2 →